5 Times Winnie the Pooh Dropped Serious Business Knowledge

winnie the pooh small business

Just kidding. Pooh can never get enough honey. And if you can’t get enough money, check out these surprisingly sound business tips from the bear himself.

Winnie the Pooh’s adventures through Hundred Acre Wood conjure thoughts of his childlike curiosity, his creative rhymes and hums, and his insatiable love for “hunny.”

Although we don’t typically think of Pooh Bear as wise, authors have used his wisdom (and the wisdom of his friends) as entry points to a range of deep thinking – from Taoism to the philosophies of Plato, René Descartes, and Friedrich Nietzsche.

Online sellers and small business owners might also benefit from the wisdom of Winnie the Pooh… and Tigger too!

Pooh Bear’s philosophical bent is owed to the character’s creator A.A. Milne who was born on January 18, 1882.

In honor of Milne, here are five lessons on small business from Winnie the Pooh.

Winnie the Pooh on Having a Plan

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Always watch where you are going. Otherwise, you may step on a piece of the Forest that was left out by mistake.

Winnie the Pooh was the ultimate wanderer. But even as he meandered from one end of Hundred Acre Wood to another, he kept his eyes on the path.

Although building a successful small business requires more long-term planning than that, it also requires a Pooh-like focus on the immediate path forward.

It requires adaptability to challenges and opportunities we didn’t foresee when starting out.

Piglet on Differentiation

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The things that make me different are the things that make me.

Piglet was a unique soul to be sure and he recognized that his uniqueness was key to who he was.

Your small business is unique as well. No one makes the products you make. No one was inspired to start a business exactly as you were. And, unlike the big-box store down the street, you’re a true neighbor to your customers.

Find the stories that highlight your unique position in the market and share them with your prospects and customers.

Eeyore on Embracing Your Shortcomings

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It’s not much of a tail, but I’m sort of attached to it.

When I was in my MBA program, we were told that there were no such things as problems. There were only weaknesses to overcome and threats to defend against.

Eeyore’s tail wasn’t mighty but he seemed pretty content with that fact. Your business has limitations. Embrace them and keep moving.

Winnie the Pooh on Priorities

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And really, it wasn’t much good having anything exciting like floods, if you couldn’t share them with somebody.

As entrepreneurs, it’s easy to get lost in our work, especially during the holiday ecommerce crush.

Although we can – and probably should – grind it out in November and December, January is a time to refocus on what’s most important in our lives. Here are my friend Nicole Cottrell’s five biggest tips for entrepreneurs in love.

Christopher Robin on Staying Strong

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Promise me you’ll always remember: You’re braver than you believe, and stronger than you seem, and smarter than you think.

As a small business owner, you are a member of an elite club. How often have you heard variations of: You’re living the dream or I wish I had the courage to do that?

In other words, you kick ass. When the going gets tough, remember the words of Christopher Robin to Pooh Bear.

You’re braver than you believe. You’re stronger than you seem. You’re smarter than you think.

Now, go get it!

How have you been inspired by Winnie the Pooh?

About the Author

Matt Simpson

Matt is a freelance writer for The DRIVE blog with expertise in digital marketing, social media, and copywriting. He's active in the #yesphx startup movement and has been recognized by AdWeek, Mashable, and more for digital innovation. Visit Matt's website or follow Matt on Twitter.


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